Anon rubbed the sleepiness out of his eyes as he walked back to his house. The soft glow of the sun rising on a new day cast long shadows over the entirety of Ponyville, making the lazy morning feel that much more comfortable and quaint as he walked alone. All the same, a thunderous chorus of confusion raged in Anon's mind, making his brow furrow.
Somehow, some way, not only once, but twice in a single day, a mare downright threw herself onto him in a lustful frenzy that ended with them sexually satisfied, passed out, and covered in both his and their sexual fluids. While his romp with Rainbow was anything but ordinary, he couldn't deny that he'd harbored lustful feelings for the rainbow-maned mare for quite some time, even if he knew she didn't like him in a romantic way.
So imagine his shock when she suddenly thrusted herself upon him, eagerly shoving her tongue down his throat and giving herself to him not just freely, but insistently. While the aftermath of such a lewd encounter was surely something he hadn't been looking forward to- not just because of the awkwardness, but because of the potential change in their relationship it rightly would have brought- he didn't even get a chance to ponder that, as Roseluck stumbled onto him right after the fact.
Anon kicked a rock as he walked, his head shaking as he recalled just how brazenly and sensually the mare had given herself to him. One moment, she was the shy and meek mare that all of Ponyville knew, and the next, she was a sex-crazed slut that wanted nothing more than for him to pin her down and breed her. Just reminiscing about the thought had little Anon Jr. springing up for attention, though Anon ignored his more basic urges for the moment.
While the prospect of Rainbow suddenly developing feelings for him was certainly fantastic news, the thought of Roseluck also deciding that she wanted a piece of him was absolutely thrilling. Even if he didn't want to admit it, Anon could not deny the fact that having two beautiful mares to call his own was a particularly invigorating fantasy of his. All the same, he still couldn't wrap his head around the why both of these mares suddenly decided to show him how much they liked him.
Why? Why now? Why not sooner? Was it just because he couldn't go home and they wanted to wait for him to come to terms with it? These questions raged through Anon's head as he finally arrived back at his quaint little apartment at the opposite side of town. Fortunately, at the early hour he'd left at, there were perilously few ponies out and about to start questioning him or inquire about his whereabouts the previous day.
As Anon unlocked his door and headed inside, he knew that there was no way both mares wouldn't be searching for him soon enough, likely to ask him why he'd left them both after their sensual experiences. Loathe as he was to admit it, he still couldn't really find an answer. Something about the way the mares just suddenly threw themselves at him just felt... wrong. No matter how much he tried to chalk it up to his luck finally changing for the better, or to some kind of divine intervention, something about the way both Rainbow and Roseluck had acted felt off.
Shaking his head as he ascended the stairs to his bedroom, Anon decided to shelve that particular point of discourse until the mares themselves arrived at his house to speak to him, or until he saw them again on his usual day to day routine. While he did have work coming up in a few hours, he found himself restless and unable to focus on the daily tasks Pinkie and the Cakes were sure to ask of him.
So, with little else to do for the next few hours, Anon decided to do the only thing that he could in his apartment: clean. The interior of his little hobble was a pigsty, for lack of better words. Anon quickly took to picking up his scattered clothing and throwing them all into the washing machine. Yes, somehow despite their lack of electricity, ponies had managed to create washers and dryers. Anon could not understand it, yet he was grateful for it all the same.
With that finished, he turned his attention to doing the dishes, however before he could step into his kitchen, a loud crash and bang reached his ears from outside. Anon frowned as he glanced over toward the source of the noise, then over to the clock on the wall.
Anon sighed heavily, "Mail time... Derpy, what did you break now?" He wondered aloud, abandoning his task of doing the dishes and heading over to the stairs.
Upon exiting his domicile, Anon was greeted by a peculiar and amusing sight. The soft gray pegasus mailmare was not only stuck in his mailbox, but somehow, someway, managed to completely shove her head and upper torso all the way through until it was sticking through on the other side. Her legs and wonderfully doughy flanks hung out the back of the mailbox, which just so happened to be angled straight toward him, giving him a perfect view of Derpy's tight ponut and darker, supple lower lips as her blond tail swished to and fro in her attempt to escape.
Anon heard several grunts and groans as the mailmare tried everything in her power to free herself from the prison she suddenly found herself in, but all of it was to no avail. So it was with a heavy sigh that Anon stepped over to Derpy's side, finally breaking her attention from her situation and directing it over toward him.
"Oh! H-hi Anon! Good morning! I've got your mail!" Derpy chirped, a nervous smile on her face as her cross-eyed amber gaze looked at both Anon and the ground, respectively.
Anon crossed his arms, "Derpy... how?" He deadpanned.
Derpy's ears splayed back against her skull as her head hung low and her eyes both fell to the ground, "I... I just don't know what went wrong." She muttered.
Anon rolled his eyes, "Derpy, this is the sixth time since I moved her that you've managed to break or crash into my mailbox. If you weren't such a sweetheart, I'd have half a mind to be upset with you." He scorned, though it was clear in his tone that he was more amused than upset.
"I know... I'm sorry," Derpy replied, before giving Anon a hopeful look ,"Think you could help me out, Anon?"
Anon let out a flippant sigh before walked over to the front of his mailbox and grabbed the slightly pudgy mailmare by the forelegs. He braced his foot against the post his mailbox rest upon and gave a firm yank. Despite the tin mailbox groaning from the sudden added pressure, Derpy simply refused to budge. Her hind legs kicked uselessly as she tried to squirm and wiggle her way free, but it was to no avail. Despite both of their efforts, even after several minutes of pulling and squirming, Derpy was still stuck.
"Damn, Derpy. How'd you get so stuck this time?" Anon asked, taking a moment to catch his breath.
"I was flying into to deliver your mail and... well... I kinda got distracted." Derpy sheepishly admitted.
Anon snickered, "So you crashed into this thing at full speed? I don't think I'm gonna be able to get you out of there without breaking the mailbox open, Derps." He shook his head as his hands rested on his hips.
"B-but, I have a lot more deliveries to make today! Here, try pushing me out the other way." Derpy suggested, already wiggling to free herself.
Anon shrugged and leaned forward, placing his hands on either side of Derpy's wither. Bracing his legs against the ground as best as he could, he pushed with all his might, while Derpy once again flailed uselessly with her hind legs. After a few good shoves, the wooden post that the mailbox rested on groaned and creaked, its frame bending against the forces being applied to it. Despite the weakening structural integrity of the mailpost, Derpy was starting to slip out slightly, a fact that both of them were happy for until the wooden post gave a small *snap*.
"Oh shit." Anon stated, suddenly abandoning his efforts to push Derpy through.
"W-why'd you stop, Anon?" Derpy questioned, finally able to move one of her wings slightly.
"We're gonna break the mailbox off the post if we keep this up." Anon explained, catching his breath from the slight exertion.
"Can you pull me from the other side? You can brace your leg like you did earlier, that way." Derpy suggested, giving him a winning smile.
Anon pursed his lips as he glanced back at the plush, supple cheeks that made up Derpy's flanks, all kinds of provocative scenarios playing in his head as the prospect of getting to stare right into her most sensual treasure reared its head. Truth of the matter was, he'd always had a soft spot in his heart for the thick-thighed mailmare, not just because of the perfectly round shape of her delicious asscheeks, but also because she was genuinely nice and well-meaning, even if she did crash into his mailbox entirely too often.
"Uh, a-alright, Derpy." Anon agreed, walking around to the other side of the mailbox and coming face to face with what the pegasus mare had to offer.
Much as he wanted to respect her privacy, there simply was no way in Hell that Anon could look away from her tight ponut and perfectly tear-drop shaped pussy. Her tail even appeared to swish out of the way to give him a perfect view of her treasure, almost as if she were tempting him on purpose, but as per usual with the slightly ditzy mare, she was simply humming a tune to herself and dancing along to her quiet beat, at least, as well as she could with how stuck she was.
Anon braced his leg against the mailpost once more, his hands grabbing both of Derpy's hind legs around the knees as he prepared to pull. This, of course, only pushed his face mere inches away from Derpy's slit, and the sweet, tangy scent of her lower lips quickly assaulted his nostrils.
"Uh, you ready?" Anon asked, quickly shaking the thoughts that were filling his head away.
"Go for it, Anon!" Derpy chirped, wiggling her flanks slightly.
Lord help me. Anon thought to himself, watching as Derpy's asscheeks hypnotically swayed back and forth in front of his face.
With consent assured, Anon gave a good tug on Derpy's legs, earning another groan of protest from the mailbox. He grit his teeth as he pulled, over and over, the morning sun slowly rising and bathing them both in its warm light. Progress was slow, meaning that for every inch Anon managed to squeeze Derpy out of the mailbox, almost five minutes of strenuous pulling and grunting were required.
Naturally, in the morning heat of a quickly approaching summer day, Anon began to perspire as he tried everything in his power to free Derpy from her prison. Slowly but surely, he managed to free her barrel, and then her withers, leaving nothing more than just her head stuck in the mailbox. Anon continued to pull, beads of sweat dripping from his brow as he tried, with all his strength, to free the mailpony. Finally, with her forelegs pushing against the frame of the mailbox, and Anon pulling for all he was worth, on her hindlegs, Derpy's head slipped out with an audible *pop*.
Unfortunately, with no more immovable object to contain the unstoppable force that was Derpy and Anon, the pegasus mailmare was sent sailing right into Anon's her weight and inertia catching him completely off guard and knocking him to the ground.
Whether it was by luck or cruel fate, Anon landed on his back, while Derpy's rear landed squarely on his face, completely entombing his head in her doughy, pudgy flanks. As for her, Derpy's head came to a rest right on Anon's lower abdomin, her muzzle landing precariously close to Anon's crotch as the sweat accumulated all over his torso soaked into her fur.
While her head was facing the opposite direction for the entirety of their encounter, Derpy's sinuses were easily able to pick up on the increasing levels of Anon's salty pheromones' as he had worked to free her. Despite herself, she couldn't help the excitement and lust that had wormed its way up her spine and moistened her lower lips to the point of dripping; Lower lips that were now completely encasing Anon's nose in their hold and coating his face in her nectar.
While ordinarily, she'd be embarrassed beyond words, the way Anon's nose rubbed up against her clit while she was bathed in the salty scent emanating from Anon's crotch, had her panting like a dog, her tongue lolling out of her mouth to collect even more of Anon's smells into her senses.
"Umghsh Derphee?" Anon's muffled voice reached her ears as Derpy unconsciously rubbed herself against his face.
The sudden vocalization, however muffled it may have been, accompanies with a tap on her generous flank, snapped Derpy out of her trance and made her sit up.
"Oh-Oh my Gosh! Anon! Are you okay!?" Derpy questioned, turning around so fast that she managed to catch the string of her arousal falling away from Anon's face and her moist cunt.
Anon licked his lips, silently savoring the taste of Derpy's essence, before quickly shaking his head and wiping the remainder of her fluids from his face, "Uh... y-yeah. I'm good, Derps." He replied, awkwardly.
While Derpy's face was already flushed with her arousal, the realization of what she'd done made her cheeks burn bright with embarrassment as well, though she couldn't help but feel a hint of excitement creep up her spine at the lack of a disgusted response from Equestria's only human.
"You, uh... got a little sweaty there, Anon." Derpy offered, both in a bid to change the subject and attempt to convince the man that he hadn't just sampled her snatch.
Anon looked down to his shirt to see that he had indeed sweated up quite a bit from the exertion of trying to free her from his mailbox. His clothing clung to him with the excess weight of his perspiration, and even though the morning sun was warm, he couldn't help but notice that he was especially flushed from the explicit encounter with Derpy's rear end.
"Uh, yeah... I should probably go inside and get change. Glad you're okay, Derps." Anon offered, getting to his feet.
Suddenly, and surprisingly to both of them, Derpy bolted over to his door and opened it for him, "Here! Let me help! I-it's my fault in the first place for crashing into your mailbox... it's the least I can do." She candidly offered, giving him an inviting- if a bit suggestive- smile.
Anon paused for a moment, both to consider her offer and to adjust to hide the semi he was sporting. Once he was ready, he gave a nervous, yet hopeful nod to the mailmare.
"Uh, sure, Derpy. That's really nice of you to offer." He smiled, heading to the front door.
"Don't mention it, Anon!" Derpy chirped, holding the door open for him as he entered.
As Anon ascended the staircase back up to his apartment, Derpy followed closely behind, her nostrils repeatedly flaring as she huffed his scent again and again. She wasn't inconspicuous in the slightest, but Anon's brain was too excited with the prospect of getting to taste her folds again to consider what she might have been doing. Within a minute, they arrived at Anon's floor and he opened the door to let Derpy inside.
Without giving Anon so much as a chance to usher her inside, Derpy leapt on him, tackling him to the ground as she mashed her lips against his, her mind all but lost to her lust. While Anon was taken by surprise from the sudden amorous assault, he was starting to get used to making out with attractive mares, and quickly responded by shoving his tongue against hers. Derpy moaned into his mouth as she tasted not just his salty flavor, but her own tangy taste on his tongue as well.
Derpy rubbed her dripping cunt against Anon's thigh, dry humping him as she continued to assault his tongue with her own, the lewd noises of their sloppy make-out session drowning out the sounds of the outside world. The door soon closed behind them, completely silencing the world around them and limiting them only to each other. This had the unintended side effect of completely sealing Derpy off from fresh air, as no windows were open in the slightly warm abode.
The scents and pheromones' of Anon's domicile quickly flooded Derpy's senses until there was simply nothing else there but him. His scent. His essence, and she wanted nothing more than to be completely smothered in it.
So she did just that. With a quick break in the kiss, Derpy slid down Anon's chest until she was able to nudge her way under his sweat-slicked shirt. She licked a trail all the way up his stomach to his chest, capturing all of his sweet salty goodness on her tongue along the way. Anon let out a soft moan as Derpy trailed all the way up to his collar, her tongue ravishing his chest and abdomen all the while.
Not one to sit out of the action, Anon reached around with his hands and kneaded the doughy flesh of Derpy's flanks. His thumbs rubbed circles over her bubbly cutie marks, each touch sending a wave of pleasure through the sensitive skin. Anon could hear the desperate panting of the mare atop him as she practically suffocated herself under his shirt, the sound turning him on even more than he already was. He moved to remove his shirt to allow for more mobility, but a sharp cry from the dull gray pegasus made him freeze.
"No! Keep it on!" She cried, before resuming her licking and grinding with earnest.
While the request was certainly strange, Anon's brain had little time to think or ponder such matters as he had a horny mare on his chest to handle. Throwing aside any concerns that may have been brewing in his head, Anon reached down and shuffled his shorts off, exposing his absolutely throbbing cock. As if with some sort of sixth sense, Derpy knew exactly what he was doing and where his cock was, despite her attention being focused elsewhere. She instantly positioned her posterior directly over his shaft, rubbing her dripping lips against his cock and coating it with her fluids.
The supple, sublime kiss of Derpy's lower lips made Anon groan in pleasure as she teasingly rubbed all the way up to the tip of his shaft, and all the way back down to the base. With how badly she was leaking, his entire manhood, sack, and groin was quickly slathered in her needy essence within a minute. Yet, when she finally appeared ready to spear him into her folds for good, she hesitated, as if struck with a moment of clarity.
"U-uh... Derpy?" Anon asked, no longer feeling any stimulation from the mailmare.
"I-I need you inside me, Anon... b-but..." Derpy managed, her breath coming in husky, ragged pants.
"But what? Derpy?" Anon asked, his own chest heaving in excitement.
"I-I already have a foal, Anon... I-I can't... handle another right now." Derpy replied, squeezing her eyes shut as if the mere thought of concentrating was taking all her strength.
"D-do you want to stop?" Anon asked, fearfully.
"No!" Derpy cried, suddenly darting forward and kissing him.
A desperate battle of their tongues started anew, though it was much shorter lived than before. After less than thirty seconds of shoving her tongue into Anon's mouth, Derpy suddenly threw her head back, gasping for air as her head popped out the same hole as Anon's on his shirt.
"M--my plothole. Buck me in my plothole, Anon... Please!" Derpy begged, biting her lip as she enticingly rubbed her rapidly winking clit against the tip of Anon's shaft once more.
Without a moment's hesitation, or thought to argue that it wasn't even possible for him to knock up a mare, Anon eagerly nodded. That was all Derpy needed to quickly set about lining herself up with Anon's tool. With his help, the mushroom-tipped head of his shaft quickly made contact with her tightly puckered anus. The lubrication applied from her smothering his cock in her juices did more than enough to facilitate the initial penetration, and albeit with a glacial pace, Anon's cockhead slowly speared its way into her as Derpy sat her hips down atop his pelvis.
Both man and pony let out audible groans of pleasure as inch after inch of delicious man-meat stuffed its way into Derpy's rear end. While Anon had never considered himself a big fan of anal, the absolute scorching inferno of heat and pressure that was Derpy's ponut had him absolutely hooked within microseconds. Each clench of her muscles made her insides tighten around his cock, almost like a boa constrictor coiling around him and milking him for everything he was worth. The torturously slow penetration had both of them seeing stars until finally, with a meaty *thump*, their hips collided, and Derpy's tongue lolled out of her mouth.
"Oh my... Celestia..." Derpy moaned, flexing her ass and rubbing her clit against Anon's groin.
"Uh... f-fuck... Derpy." Anon muttered, grabbing a handful of her plush flanks with each hand.
Without another word, Derpy slowly lifted her hips until just the tip of Anon's wonderous shaft remained inside of her, before slowly sitting back down onto him. The motion, slow and steady as it might have been, was undeniably euphoric, sending wave after wave of pleasure up both of their spines. Each thrust in was met with the clenching and subsequent constricting of Derpy's vice like walls around Anon's staff, while each retreat was met with complete relaxation, allowing him to quickly slide out.
The smooth, ribbed texture of Derpy's asshole was absolutely breathtaking as Anon was properly ridden by the beautiful little mailmare. Her wings strained against the fabric of his t-shirt, desperately trying to flap and cool her off as she panted with the exertion of throwing her ass down on Anon's pillar of manhood again and again. Her every thought was filled with nothing but the absolutely orgasmic scent permeating every facet of her senses. All she could taste, touch, smell, see, or hear was Anon and his lovely, salty scent, and she couldn't get enough of it.
Her pussy clenched again and again on a member that simply wasn't there, but the sensation of Anon's cock absolutely destroying her plothole was more than enough to wrack her with pleasure. She could feel his behemoth of man-meat through the walls of her pussy, his every thrust assaulting her g-spot from the other side and driving her closer to orgasm.
Anon, meanwhile, was gasping and groaning in ecstasy as his shaft was completely engulfed in scorching warmth and vice-like tightness. His hands squeezed Derpy's asscheeks so tightly, spreading them apart and pinching them between his fingers so viciously that the poor mare cried out in pain and pleasure from the rough treatment. Sensing blood in the water, Anon took the opportunity to slap her meaty ass with one hand, making the plump little mailmare moan as her tongue lazily lapped at his chest again.
"Oh, Anon... oh, Anon..." Derpy mumbled, her own movements devolving into uncoordinated undulating as Anon's cock absolutely fucked her silly.
"Derpy..." Anon replied, panting for breath as thrust his hips to really pound away at Derpy's ponut.
The rapid fire pounding that her rear end was assaulted with quickly drove Derpy toward the point of release, and with a climactic howl, she threw her head back as far as she could inside of Anon's shirt. Her velveteen walls convulsed again and again on a member that wasn't even there as her juices flooded Anon's groin. Squirt after squirt of marecum flushed all over Anon, flooding his underwear with her essence and dripping down into a puddle all around them both.
The tightly constricting walls of Derpy's insides quickly pushed Anon past the edge as well, and through grit teeth, he slammed his hips against hers and held her in place as his cockhead erupted inside of her. Anon's eyes closed in ecstasy as he fired nearly a dozen heavy ropes of his thick human seed deep into Derpy's rear end, her juices flooding his lap the whole while.
Together they bathed in cataclysmic rapture, both moaning and groaning as their orgasms gradually subsided. Slowly, but surely, the two of them came down from their high. Derpy let out one final moan of happiness before flopping unceremoniously onto Anon's chest. Anon watched as the form under his shirt rapidly rose and fell with her panting breaths. Anon's own torso heaved from both the exertion and from the weight of the mare on his chest.
"H-holy... shit, Derpy... that was amazing..." Anon breathily muttered, reaching over and rubbing Derpy's back through his shirt.
The only response he received was more muffled panting from the pegasus mare. He chanced a peak down his shirt to see if she was still alright, only to be graced with the sight of her closed eyes and clearly unconscious face.
"Ah... yeah, that's been happening a lot, lately." Anon stated, laying his head back against the floor.
After a few more minutes of blissful quiet, only the sound of both man and pony breathing, Anon finally decided that the floor was not as comfortable as a bed, and elected to move. He gingerly sat up, cradling Derpy in his shirt as he did and keeping his length entombed in her asshole as he carried her over toward the bedroom. As gently as he could, Anon slipped the shirt off of Derpy's body and deposited her on her back. The mattress creaked ever so slightly as it accepted her weight, and with a final *pop*, Anon slid his deflating erection out of Derpy's thoroughly fucked hole.
A torrent of cum dribbled from her gaping ponut, absolutely soaking into her tail and dock as the snoozing mare laid on her back, her forelegs curled up to her chest as she dreamed of something that put a smile on her face. Were it not for the absolute glazing Anon had given her rear end, he'd be inclined to admit that she was particularly adorable, laying on her back without a care in the world.
It was a sight that warmed his heart, and with a gentle motion, he covered her with his sheets, allowing the ditzy pegasus to snuggle further into his bed as she rested peacefully after such an exciting but exhausting endeavor. With that taken care of, Anon turned and headed toward the shower, taking a moment to glance at the clock on the wall before he stepped inside.
"Shit... gotta get over to SugarCube Corner in about half an hour... hopefully Derpy wakes up by then... eh, if not, I'm sure she'll be fine." He shrugged, before turning on the hot water.
As relaxing as the shower was, Anon couldn't help but feel a wave of excitement rush up his spine. Three mares had thrown themselves at him within a time span of twenty four hours. If things kept up at this pace... who knows what the future could hold?
Author's Note
Heya everyone. We have done it. We sexed the muffin mare! This one was a lot of fun to write and I hope you all enjoyed it as much as I did. Derpy of course, deserves nothing but the best, after all.
As usual, please leave your suggestions for the next mare in the comments below! I'll have my partreon vote on who they wish to have Anon plow next, and next month, we shall have another story!
If you'd like to support me on Patreon and maybe vote in the next poll, please consider joining! https://patreon.com/user?u=4398966
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